Short enantioselective approach to substituted triazolopyridazines from [(S)R]-1-(1E, 3E)-1-p-tolylsulfinyl-1,3-pentadiene

Carreño, M. Carmen; Cid, M. B.; Ruano, JoséL. García; Santos, Mercedes

doi:10.1016/s0040-4039(97)10776-6

Cited by 21 publications

(13 citation statements)

References 15 publications

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“…For example, the diene substituted with a pseudoephedrine-derived oxazolidine 170 gave the product in only modest stereoselectivity when reacted with benzyl nitrosoformate ( 171 ) [130]. On the other hand, the reaction of the chiral 1-sulfinyl diene 174 was found to be completely regio- and stereoselective when reacted with the same dienophile (Scheme 34) [131–132]. …”

Section: Reviewmentioning

confidence: 99%

Stereo- and regioselectivity of the hetero-Diels–Alder reaction of nitroso derivatives with conjugated dienes

Brulíková

Harrison

Miller

et al. 2016

Beilstein J. Org. Chem.

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SummaryThe hetero-Diels–Alder reaction between a nitroso dienophile and a conjugated diene to give the 3,6-dihydro-2H-1,2-oxazine scaffold is useful for the synthesis of many biologically interesting molecules due to the diverse opportunities created by subsequent transformations of the resulting 1,2-oxazine ring. This review discusses the rationale for the observed regio- and stereoselectivity and the methods developed in recent years used to control and improve the stereo- and regioselectivity for the synthesis of 1,2-oxazine scaffolds.

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Section: Reviewmentioning

confidence: 99%

Stereo- and regioselectivity of the hetero-Diels–Alder reaction of nitroso derivatives with conjugated dienes

Brulíková

Harrison

Miller

et al. 2016

Beilstein J. Org. Chem.

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“…This, in turn, places the chiral moiety of 1substituted acyclic dienes spatially distant from the bulk of the incoming nitroso dienophile. Nevertheless, chiral acyclic dienes, such as chiral N-dienyllactams 49, [72,73] pseudoephedrine-derived oxazolidines 50, [74] and chiral 1-sulfinyl dienes 51 ( Figure 8) [75,76] have been successfully used in asymmetric nitroso HDA reactions.…”

Section: Chiral Dienes In Nitrosocarbonyl Hda Reactionsmentioning

confidence: 99%

The Nitrosocarbonyl Hetero‐Diels–Alder Reaction as a Useful Tool for Organic Syntheses

Bodnar¹,

2011

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Organic transformations that result in the formation of multiple covalent bonds within the same reaction are some of the most powerful tools in synthetic organic chemistry. Nitrosocarbonyl hetero-Diels–Alder (HDA) reactions allow for the simultaneous stereospecific introduction of carbon–nitrogen and carbon–oxygen bonds in one synthetic step, and provide direct access to 3,6-dihydro-1,2-oxazines. This Review describes the development of the nitrosocarbonyl HDA reaction and the utility of the resulting oxazine ring in the synthesis of a variety of important, biologically active molecules.

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“…114 This process involves a tandem Diels-Alder cycloaddition/sulfoxidesulfenate rearrangement and trapping of the intermediate sulfenate. …”

Section: Scheme 56mentioning

confidence: 99%

Recent developments in chiral non-racemic sulfinyl group chemistry in asymmetric synthesis

Hanquet¹,

Colobert²,

Lanners³

et al. 2003

Arkivoc

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Chiral sulfinyl groups have been widely used in organic synthesis as a stereo-and enantiodirecting functionality and the high efficiency of the selectivity has received much attention in recent years. In this review we wish to cover the work published in the literature since 1996. The participation of a chiral sulfinyl function in a wide range of reactions as well as the application of these methodologies to the synthesis of natural products are reported.

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Short enantioselective approach to substituted triazolopyridazines from [(S)R]-1-(1E, 3E)-1-p-tolylsulfinyl-1,3-pentadiene

Cited by 21 publications

References 15 publications

Stereo- and regioselectivity of the hetero-Diels–Alder reaction of nitroso derivatives with conjugated dienes

Stereo- and regioselectivity of the hetero-Diels–Alder reaction of nitroso derivatives with conjugated dienes

The Nitrosocarbonyl Hetero‐Diels–Alder Reaction as a Useful Tool for Organic Syntheses

Recent developments in chiral non-racemic sulfinyl group chemistry in asymmetric synthesis

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